The First Time
by DC Derringer
Summary: How did Dean and Sam manage to lure Castiel into their depraved little sex life? Apparently, it wasn't that difficult.


Title: The First Time

Pairing: Dean/Sam/Castiel

Rating: NC-17

Word Count: 1,300

Warnings: oral, anal, virginity, airtight

Summary: Winchester Affection Verse. Castiel's first time with the Winchesters.

AN: I was wondering how the Winchesters managed to lure Castiel into their depraved little love life. Apparently, it wasn't very difficult.

The first time, Castiel thought Dean was in danger. He could sense the man was in pain and rushed to his side. He found him held down under Sam, and felt his righteous anger rise up at the sight of the two brothers brought to this. With a wave of his hand, he flung Sam across the room.

"Don't you hurt him," Castiel had growled, prowling over to Sam to ensure the man was fully incapacitated.

"Cas! What are you doing?" Dean yelled, standing by Castiel's side and pulling him around so that they were face to face.

"If you two wish to argue, do so. But I will not allow Sam to hurt you."

"Argue?" Dean gave him a puzzled look, and then suddenly he was laughing. Castiel was startled, and more so when he realized Sam was laughing as well, even though he was still crumpled up on the floor where Castiel had flung him.

"We weren't exactly arguing, Cas. We were, you know…" Dean gestured to his own body, and finally, Castiel realized that both men were naked, and apparently, sexually aroused. He felt embarrassed, but then also, incredibly curious and intrigued.

"You were in pain…" Castiel insisted. He had been quite certain of that, sensing Dean's discomfort through their bond.

"That's because Dean's a sissy," Sam said, standing up finally. "Can't take it like a man."

"Take what?" Castiel asked, curious.

Both brothers shared a look, one that spoke of a thousand private and secret words, shared between them all their lives, in a language that only these two special men could understand. Castiel could only ever hope to begin to understand the looks they shared.

"We'll show you," both brothers said in unison.

Without protest, Castiel allowed the two men to lead him over to the bed, and push him down gently. He let them undress him, peeling off the layers of his human clothes that he never thought about, leaving him naked in his human body for the first time. Castiel wondered idly why humans were so ashamed of their own nudity, especially with the casual way that Dean and Sam carried themselves in their natural skin.

It started with kissing, surprisingly gentle and wet. Dean claimed his lips, and Sam worked on his neck, causing suction that he would realize later left red bruise-like marks on his skin. Next there was touching as the two men ran their hands all over him, focusing on certain parts of his body with extra attention. They plucked at his nipples, and dipped their fingers into his navel. They tugged the hair on his head, and more gently, the hair between his legs, both of which made him gasp and groan. They grabbed his ass, a little roughly, and pulled his cheeks apart to tease at the small entrance there. That made Castiel gasp even more loudly.

"This is your first time, right Cas?" Sam asked, crowded against Castiel on one side. Dean pressed up against him on the other.

"Yes," Castiel said, blushing slightly from the confession, unseemly as it was since he was a trembling pile of desire trapped between two very visibly aroused men who seemed very interested in him all of a sudden.

Castiel watched as the two men shared another look, and then a smirk. Over his chest, they each held out a hand, counted to three and then stuck out two different hand signals, one pair of scissors, one piece of paper. Dean cheered with joy over his choice of scissors, while Sam just rolled his eyes. He was smiling too, though.

Dean sat up and tugged Castiel up with him. Easily, he moved Castiel's pliant body onto his hands and knees, kneeling on the bed with Dean behind him, and Sam in front of him.

Dean's fingers plied between Castiel's cheeks again, like they had earlier when he explored, but now his fingers were wet and slippery. One finger moved inside Castiel's body with surprising ease, leaving Castiel gasping from the unique, invasive pleasure.

A touch to his cheek, and Castiel turned his head. His nose bumped against Sam's cock, and the larger man laughed. Sam held his cock, pressing it insistently against Castiel's mouth, smearing his lips with pre-come. Slowly, Castiel understood the request and opened his mouth, taking the tip into his mouth to taste the salty fluid.

With soft words of encouragement, Sam guided Castiel through his first cock sucking, praising him and moving slowly as he adjusted and learned what to do. Behind him, Dean worked his entrance open, sliding two slippery fingers and then three into his body. He moaned at the sensation of slowly being opened, of having these men inside him. The taste of Sam's cock and the feel of Dean's fingers were intoxicating. He'd never known such a visceral pleasure could exist.

He also didn't expect it to get any better. He moaned with disappointment when Dean withdrew his fingers, leaving him empty. Both men laughed at him, full throated laughter, that left him feeling infected and happy, not embarrassed as he should have been.

The emptiness was soon filled though, and Castiel cried out from the feeling. He looked behind, and saw Dean burying his cock deep into his ass, and now he understood why Dean had cheered at winning the game with Sam. His heart hammered at the thought that he was the prize for their game.

It was hard to concentrate on Sam's cock with Dean's cock working in and out of him, hitting some small secret spot inside each time that made lights explode before his vision. But Sam took over, and started thrusting into Castiel as well, so that both men were pistoning in and out of him, filling him up over and over again, forcing pleasure into his body.

There was only a quick warning from Sam, and then Castiel had to prepare for the rush of semen in his mouth, thick and salty, and tasting like the essence of Sam. He swallowed most of it, but some of it slipped down his chin. When Sam pulled out of Castiel's mouth, he moaned at the sight of him and leaned down to claim his lips, forcing his tongue in to taste himself in Castiel's mouth.

Behind, Dean still worked in and out of him, and clinging to Sam for support, Castiel pushed back to meet him, rolling his hips to help seek that pleasure that was building up in his groin, a high pinnacle he thought he would never reach.

There was a burst of heat inside him, and Dean groaned loudly, his hips jerking harder for a moment, and then going still as he pulsed and throbbed, and filled Castiel up from the other end with his own semen. Castiel whimpered from the sensation, imagining the essence filling him up, only to leak out again when Dean slid free.

The two men flipped him over, onto his back, and observed the erection bouncing freely against his belly. They shared another look and licked their lips in unison. Both bent down together, with Sam latching his mouth to Castiel's cock, and Dean sucking Castiel's balls into his mouth. Castiel cried out and squirmed fitfully beneath them, the pleasure against his already sensitive and overrun flesh overwhelming.

A minute passed, and Castiel experienced his first orgasm, at the hands, mouths, and cocks of Sam and Dean Winchester. He exploded first into Sam's mouth, who gulped down a few spurts, and then his cock was passed to Dean, who gulped down the last of it, and teased at the slit to suckle out any remaining drops.

Sweating, panting, and completely finished, Castiel was sandwiched between the two men on the bed, the three of them barely fitting on the narrow motel bed without squeezing so tightly together. Anyone else would have found it suffocating, but Castiel felt that this was just a special brand of Winchester affection, not meant for anyone else, and only recently, himself.


End file.
